Reductive amination of acetals by anilines in the presence of triethylsilane and iodine

Xue Lin Zhang; Pan Yu; Yong Wei Wu; Qin Pei Wu; Qing Shan Zhang

doi:10.3184/174751914X13946178288518

Reductive amination of acetals by anilines in the presence of triethylsilane and iodine

Xue Lin Zhang, Pan Yu, Yong Wei Wu, Qin Pei Wu^*, Qing Shan Zhang

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I₂ and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.

Original language	English
Pages (from-to)	261-264
Number of pages	4
Journal	Journal of Chemical Research
Volume	38
Issue number	5
DOIs	https://doi.org/10.3184/174751914X13946178288518
Publication status	Published - May 2014

Keywords

Acetals
Alkylation of amines
Secondary amine
Triethylsilane

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10.3184/174751914X13946178288518

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abstract = "A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.",

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author = "Zhang, {Xue Lin} and Pan Yu and Wu, {Yong Wei} and Wu, {Qin Pei} and Zhang, {Qing Shan}",

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AU - Zhang, Xue Lin

AU - Yu, Pan

AU - Wu, Yong Wei

AU - Wu, Qin Pei

AU - Zhang, Qing Shan

PY - 2014/5

Y1 - 2014/5

N2 - A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.

AB - A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.

KW - Acetals

KW - Alkylation of amines

KW - Secondary amine

KW - Triethylsilane

UR - http://www.scopus.com/inward/record.url?scp=84901041507&partnerID=8YFLogxK

U2 - 10.3184/174751914X13946178288518

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VL - 38

SP - 261

EP - 264

JO - Journal of Chemical Research

JF - Journal of Chemical Research

IS - 5

ER -

Reductive amination of acetals by anilines in the presence of triethylsilane and iodine

Abstract

Keywords

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